1094435-87-6

Basic information

• Product Name: C₂₉H₃₃NO₄S
• Synonyms: C₂₉H₃₃NO₄S
• CAS NO: 1094435-87-6
• Molecular Weight: 491.651
• Mol File: 1094435-87-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: C₂₉H₃₃NO₄S(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₉H₃₃NO₄S(1094435-87-6)
• EPA Substance Registry System: C₂₉H₃₃NO₄S(1094435-87-6)

Safety Data

• Hazardous Substances Data: 1094435-87-6(Hazardous Substances Data)

Upstream product

• 21947-98-8 N-tert-butyloxycarbonyl-S-trityl-L-cysteine 
• 1585181-22-1 ethyl (R)-4-tert-butoxycarbonylamino-5-(triphenylmethylthio)-pentanonate 
• 1585181-21-0 ethyl (R,E-)-4-tert-butoxycarbonylamino-5-(triphenylmethylthio)-penta-2-enoate 
• 149910-63-4 N-α-(tert-butoxycarbonyl)-S-(triphenylmethyl)-L-cysteinal 
• 158861-38-2 (R)-N-methyl-N-methoxy-2-tert-butoxycarbonylamino-3-(triphenylmethylthio)propionamide 
• 249507-22-0 (S)-N-methyl-N-methoxy-2-tert-butoxycarbonylamino-3-(triphenylmethylthio)propionamide 
• 1094435-86-5 ethyl (S)-4-tert-butoxycarbonylamino-5-(triphenylmethylthio)pentanoate 
• 1333536-81-4 ethyl (S,E)-4-tert-butoxycarbonylamino-5-(triphenylmethylthio)-penta-2-enoate 
• 175357-57-0 tert-butyl (S)-(1-oxo-3-(tritylthio)propan-2-yl)carbamate 

Downstream Products

• 1333536-82-5 (4S)-4-N-tert-butoxycarbonylamino-5-(triphenylmethylthio)-pentanoic acid allyl ester 
• 1333536-66-5 C₂₇H₂₉NO₂S 
• 1333536-68-7 pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S,6S)-6-[(1S)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-5-(2,2,2-trichloroethoxycarbonyloxy)-3-methylhept-1-yl}ester 1-(9H-fluoren-9-ylmethyl)ester 
• 1334149-94-8 apratoxin S₄ 
• 1585181-32-3 pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S)-6-[(1S)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-3,6-dimethyl-5-(2,2,2-trichloroethoxycarbonyloxy)-hept-1-yl}ester 1-(9H-fluoren-9-ylmethyl)ester 
• 1585186-80-6 apratoxin S₁₀ 
• 1333536-80-3 C₆₂H₈₅N₅O₁₁S 
• 1585181-30-1 pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S)-6-[(1S)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-3-methyl-5-(2,2,2-trichloroethoxycarbonyloxy)hex-1-yl}ester 1-(9H-fluoren-9-ylmethyl)ester 
• 1585180-89-7 pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S)-6-[(1S)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-5-hydroxy-3-methylhex-1-yl}ester 1-(9H-fluoren-9-ylmethyl)ester 

Relevant articles and documents

MACROCYCLIC THERAPEUTIC AGENTS, METHODS OF MANUFACTURE, AND METHODS OF TREATMENT

The instant invention describes macrocyclic compounds having therapeutic activity, and the mechanism and methods of treating disorders such as autoimmune diseases, inflammation, and cancer, tumors and cell proliferation related disorders.

Systematic chemical mutagenesis identifies a potent novel apratoxin A/E hybrid with improved in vivo antitumor activity

Apratoxins are cytotoxic marine natural products that prevent cotranslational translocation early in the secretory pathway. We showed that apratoxins downregulate receptors and growth factor ligands, giving a one"two punch to cancer cells, particularly those that rely on autocrine loops. Through total synthesis, we tested the effects of amino acid substitutions, including alanine scanning, on the downregulation of receptor tyrosine kinases and vascular endothelial growth factor A (VEGF-A) and probed the stereospecificity of target engagement by epimerization of selected chiral centers. Differential effects on two types of secretory molecules suggest that the apratoxins' substrate selectivity with respect to inhibition of secretion may be tuned through structural modifications to provide tailored therapy. Our structure"activity relationship studies and medicinal chemistry efforts led to a potent inhibitor with in vivo efficacy in a colorectal tumor xenograft model without irreversible toxicity exerted by apratoxin A, demonstrating that this novel mechanism of action has therapeutic potential.